How To Flirt With Women

Dating coach Connell Barrett answers your questions on how to flirt with women, going in for the first kiss, and how to approach in the daytime.

How To Flirt With Women

I want to learn how to flirt with women better. Maybe I’m just not witty or funny enough. I know I’m doing something wrong, but I’m not sure what. Where should I start?

—Timothy, 28, Milwaukee

I’ll bet you a case of Milwaukee’s Best (the beer that got me through college, and almost got me kicked OUT of college) that the problem is your vocal tonality.

Here’s the thing about learning how to flirt with women: your tone of voice is more important than the words you say. Stop worrying about finding the magical phrase that makes women swoon (there’s no such thing) and start focusing on how you use your voice.

Your vocal tonality conveys your confidence level, or lack thereof. And to women, confidence is intoxicating. So cultivate a rich, resonant tonality. How? You can…

Record conversations with friends and listen to your voice for flaws such as “up-talking” (when statements sound like questions) and excessive ums and uhs.
When speaking in person, imagine someone is directly behind the other person and talk loud enough that “both” of them will hear you. This will help you project your voice, since chances are it shuts down a little when speaking to a woman you find attractive. (It’s a common unconscious reaction when we feel insecure).
Think of a continuum of voice tonality, from supplicating (hesitant, quiet, up-talking) to neutral/friendly (your normal voice) to commanding (drill sergeant barking orders). Seek the sweet spot that falls between commanding and neutral/friendly. This is the tonality that sounds firm and certain, yet friendly and upbeat. Here’s a visual to help:

Commanding Tonality

(this marks your sweet spot!)

Neutral/Friendly

Supplicating

Flirty “lines” are fine as far as they go, but nothing ignites a woman’s attraction for you like a confident, resonant vocal tonality.

Kiss Is On Your List

Connell, I get in my head about dating in the era of #MeToo. On first dates, should I ask the woman for permission to kiss her?

—Doug, 33, Columbus, Ohio.

Should you ask for permission to kiss her? Yes—if you’re a time-traveling knight from Medieval Europe looking for love in the present day. (Hey, that’s not a bad screenplay idea. Working title: “One Knight Stand.”)

I’m all about getting verbal consent for sexual acts. And asking a woman permission to kiss her may sound chivalrous. But it’s just not sexy.

A girl likes it when a guy can read her signals, build romantic tension, and then make the first kiss feel like it “just happened” at the perfect moment.

I want you to read the woman’s cues and look for that “Kiss Window.” With enough dates under your belt, your brain will know when to kiss. You’ll be able to “read the room.” She’ll smile a certain way, her eyes will look bigger, she’ll lean in, and you’ll hear that little voice say, “The window’s open. Go!” Obey that voice.

Seize the Day(time)!

Where I live, COVID has been defeated, and I’m ready to start meeting girls in real life. There are some total cuties at my local coffee shop. Is it OK to approach in the daytime? Or is that creepy? Maybe I just let them drink their coffee and not be “that guy.”

—Stevie, 43, Auckland, N.Z.

It’s A-OK to approach a woman in the day time—when done with charm and a confident vibe. You might be surprised how well many women respond to this.

Remember: Single women don’t want just ANY man to approach them. But they’re dying for a MAN to approach them—that is, an authentic, charming gentleman with good intentions.

Quick story. I was once at an outdoor mall one afternoon when I met Maggie. It was very early in my quest to get good at dating, so I was still battling “approach anxiety”—that feeling of churning nerves that can stop you from breaking the ice with a pretty girl. She could sense it, I think. After I got Maggie’s number, she said, as if speaking to ALL single men, “You can come right up and talk to us. It’s okay. We like it.”

Now, daytime approaching is not quite the same as going out at night to the bars. At night, alcohol tends to be glowing, and the vibe is more intense. But when the sun is out, you’ll want to be more laid back, chill. Think “friendly,” not sexual.

Use this tip when approaching, say, at a café in the daytime: Break the ice (coffee) with a G-rated compliment. Notice something innocent and non-sexual that you admire: her style, her tattoo, her choice of half-calf, double-cupped, no-sleeve, 2-pump, extra-whipped, mocha-drizzle, ramma-lamma-ding-dong coffee. A sincere, G-rated compliment will likely make her smile, say thanks, and get her thinking, “Who IS this charming, confident guy?”

Connell Barrett is a NYC dating coach helping men all over the world find the women of their dreams. Connell has appeared in publications such as O Magazine, Cosmopolitan, Maxim and more. He's also been featured on shows like Access Hollywood and The Today Show.